Total Synthesis of Rhoiptelol B

Isao Kadota, Nobuhiro Tanaka, Hiroyoshi Takamura
2018 Heterocycles  
A stereoselective total synthesis of rhoiptelol B, a diarylheptanoid isolated from the fruits of Rhoiptelea chiliantha, is described. The tetrahydropyran ring was constructed via an intramolecular allylation methodology. Rhoiptelol B (1), a diarylheptanoid having a tetrahydropyran (THP) ring, was isolated from the fruits of Rhoiptelea chiliantha in 1996. 1 This compound was also isolated from the bark of Alnus hirsuta in 2007, and found to show inhibitory activity against lipopolysaccharide
more » ... opolysaccharide (LPS)-induced nuclear factor-kB (NF-kB) activation, nitric oxide (NO) and tumor necrosis factor-(TNF-) production. 2 The unique biological activities and structural features have attracted attention of synthetic chemists. The first total synthesis of 1 was accomplished by Reddy and co-workers in 2010 via the reductive etherification of a hydroxy ketone derivative. 3 Yadav and co-workers reported two different approaches based on FeCl3 catalyzed cyclization 4 and Prins cyclization, 5 respectively. In this paper, we wish to report a stereoselective total synthesis of rhoiptelol B (1) via the intramolecular allylation of -acetoxy ether. Figure 1. Structure of rhoiptelol B (1)
doi:10.3987/com-18-s(t)57 fatcat:2ylwyirbtnd3vijc6bsh6ndzwa